Hmm, this one is rather hard. Even though I usually like the Grass type starters the best, Chikorita was one of the exceptions to that. I honestly don't know why I never used Chikorita, but it was probably because the first gym was a Flying type gym, and I didn't want to take the time and train another Pokémon to help me beat Falkner. I didn't really like Chikorita's design either, and I'm not really sure what it's even based on.
My choice the one I'd choose, though, is kind of a tie between Totodile and Cyndaquil.
Their designs were some of the best that were introduced in the second generation imo, and both of them are actually really cute.
Cyndaquil is, as it was stated a lot in the posts above, really freaking cute. Its facial expression is one of the cutest things I've seen on any Pokémon, and I loved Ash's Cyndaquil in the Animé sooo soo much. The flame on its back is also cute in some way, even though its meant to actually be threatening, or kind of show that it's getting ready to battle. So to put this simple, if anyone ever wanted to know the definition of cute, I'd just show them a picture of Cyndaquil, because I know they'll understand immediately.
While being extremely cute and all, Cyndaquill is actually a good battler too. I've gone long in the games with only Cyndaquil in my team (but it ends up evolving anyways, though ;;), and it rarely ever let me down n_n
But even with Cyndaquil being so perfect in every way, Totodile still stands up to it.
Totodile's cuteness doesn't really stand up against Cyndaquil's, but I still love the cute expressions it is capable of giving, and I consider some of its actions in the Animé cute too. But its cuteness is easily overshined by its awesomeness, and the fact that it's based on a crocodile only adds to that.
The one thing I like the best about Totodile is its amazing design. It's such a unique and colorful design that isn't shared with many Pokémon, and that is also why it was the first starter I ever chose from the second generation.
There really isn't much to say about Totodile's battling style. It isn't really anything special untill it evolves, which is really a shame when you look at all its other attributes, though it can still be a great ally depending on the opponent :)
The last thing is Totodile's personality in the animé. It was always hyperactive and it was always trying to have fun, but it also tried its best in battles, which is what made it one of my favorites of Ash's Johto team.
In the end I'd have to go with Totodile though, mainly because it doesn't really get any love, but also because I have had such great experiences with it.
